


Where's Waldo?

by QuidnamInferorum



Series: Tumblr Challenges [7]
Category: Supernatural
Genre: F/M, Reader-Insert
Language: English
Status: Completed
Published: 2017-02-05
Updated: 2017-02-05
Packaged: 2018-09-22 06:12:19
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,227
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9587411
Author URL: https://archiveofourown.org/users/QuidnamInferorum/pseuds/QuidnamInferorum
Summary: Dean and the reader have to attend a ball. Written for spnbuddywriters’ First Quarterly Challenge on tumblr! Second part will be done by deansdirtylittlesecretsblog and I will link to it once it's up.





	

**Prompt GIF:**  


There were few events in a hunter’s life where they got to dress to the nines and be surrounded by civilized company.

But, when a shapeshifter has infiltrated the family of a prominent politician, drastic times called for drastic measures.

The plan was simple: there was a fundraising gala where the plates cost more money than the average person would see in several lifetimes, the attire was black tie, and everyone spent the entire night needling each other in hopes of something interesting happening. Dean and Y/N would sneak in whilst Sam would be in the van on his laptop, speaking to them like they were in _Ocean’s Eleven_ (when she’d made the reference, Dean had called dibs on being Clooney).

They’d maxed out two or three of their credit cards buying the necessary disguises, which had been a fight in and of itself.

He’d grumbled about wearing a tuxedo, complaining about how constricting and uncomfortable it was, to which Y/N replied with “Suck it up, Winchester.”

She had managed to find a dress to pour herself into, with the help of many foundation garments. It was beautiful and made her feel like a princess or, at the very least, landed gentry.

She stood in the motel bathroom, trying to make herself as beautiful as possible with such limited resources.

Her makeup and hair as good as it was going to get, she began zipping herself into her dress. It got halfway up her back before the angle became too strange for her to do herself. She struggled a moment more before sighing heavily and resigning herself to her fate.

She opened the door of the bathroom to reveal Dean looking all… _Dean_ in his tuxedo and one arm raised, obviously ready to pound on the door and tell her to hurry up.

His eyes widened when he saw her and a smattering of pink on his cheeks accentuated the constellation of freckles that were there.

She huffed before turning around to show him her half-done up dress. “Yeah, I know, we're running late. Help me do my dress, then we can go.”

She was answered with silence. She turned to look at him over her shoulder. He was standing there, completely gobsmacked. His eyes were wide as they stared at the expanse of back she’d revealed to him. She called his name, breaking him from his reverie. “C’mon, Winchester, hurry up!”

He gave her an awkward smile, the one he brought out with a cock of his head when he wasn’t quite sure how to react.

She watched as his thick calloused fingers brushed up against the skin of her back, and she was incredibly proud of herself for not shuddering.

Her chest became slightly more compressed as the dress was zipped up, and she couldn’t be sure if her shortness of breath was due to the look that had been in Dean’s eyes or, controversially, the dress getting tighter.

“You’re all set,” he mumbled, and there was a beat of tense silence before his footsteps could be heard, moving away.

She whirled around, sighing heavily. Before she could react, he was out the door with his FBI peacoat, muttering something about waiting by the car.

_What a baby_ , she frowned.

Moments like these had been happening a lot lately: moments where the blatant sexual tension between the two of them would be thick enough to cut with a knife.

And then Dean would run away.

She was getting tired of waiting for him to make a move. She was a modern girl, what was wrong with her making the first move?

She huffed, deciding to push the thought to the back of her mind. Instead, she grabbed her ridiculously high heels from the end of her bed and ran out to join the Winchesters.

The party was in full swing by the time they arrived. Sam frowned a little, expressing a wish that they could’ve arrived a little earlier to allow him more set-up time. Dean had thrown Y/N under the bus, and she employed the phrases “fashionably late” and “shut up, Dean” several times.

They left Sam in a dark van they’d found. Dean, however, drove Baby around to the front. He’d stopped to give a lecture to the valet, threatening the man’s children and grandchildren if there was even a scratch on his car.

Y/N eventually dragged him away and up the massive steps, threading her arm through his.

As they ascended the grand staircase that looked like it belonged in Cinderella’s castle, Dean spoke. “You look beautiful, sweetheart.”

Her head snapped as she looked up at him. “Thanks…what brought that on?”

He shrugged. “Didn’t tell you earlier.”

“Well,” she smiled widely. “You don’t look half-bad yourself.”

He smirked, pleased with her response. They were led into the massive dining room. Well-dressed men and women led them to their seats along the long, ornate table. Along the middle of it were beautiful, antique candelabras, which were obviously more for show than light, if the gigantic chandelier hanging down from the cavernous ceiling was any indication.

A man that looked like a butler from an old movie, complete with slicked back hair, a black bowtie, and pristine white gloves, came over. He pulled out Y/N’s chair, mumbling a quiet “madame.” Dean shooed him away, grumbling that he had it. The server, seemingly unperturbed by the elder Winchester’s gruff demeanor, spirited away to help an older couple.

Y/N rolled her eyes. “Don’t bite the poor guy’s head off. He’s just doing his job,” she spoke softly as she sat down, smoothing her skirt.

Dean leaned down, his lips brushing against the shell of her ear in a show of faux-intimacy. “Need I remind you that we are playing a high stakes game of Where’s Waldo?”

She almost didn’t hear his words over the blood rushing in her ears. Then he pulled away and sat down in his seat beside her, and she regained her composure. “You think that, of all the people in the room, the shifter’s gonna be Mr. Carson over there?”

“He could be between people.”

“I resent that you immediately assume that it’s a boy—hang on, do shifters have genders? Do they identify as one or the other or are they fluid? Are they both?”

“You know what, next time I’m being attacked by one, I’ll ask,” Dean rolled his eyes.

“You’re a gentleman and a scholar,” she rested her hand over his and squeezed it playfully.

Dean smiled a true, bright smile. 

The fluttering in her stomach that that smile caused was definitely _not_ butterflies.

A tiny ringing bell began sounding. The hunters looked up towards the head of the table where the man of the hour sat.

The governor of New York was a man named Alexander Whitley. He was approximately seventy years old and held an astonishing resemblance to the Crypt Keeper. He cleared his throat and began to speak, “Good evening. On behalf of Jillian and myself, I’d like to thank you all for coming this evening. This night means a great deal to everyone here, and we’re honored that you decided to spend the evening with us. Now, without further ado,” with that, the host clapped his hands.

At the signal, carts entered the room like a flood. They were distributed evenly around the room, the silver domes sparkling.

Dean was practically drooling.

The servers revealed the food with a flourish. They then sped around the room, dishing up food for each guest at lightning speed.

The moment the definitely incredibly expensive food hit their plates, Dean was practically face-first into it.

Y/N kicked him under the table, but that did nothing to deter him.

She sighed, knowing that he was lost for a while, as her eyes began scanning the room.

Unsurprisingly, all the silverware was silver. Y/N had taken a moment to inspect her own set after sitting down, and they definitely seemed to be the real thing. Then again, with how lovely the rest of the house was, she’s wouldn’t be _too_ surprised if they’d cheaped out on the silverware.

Going off the assumption that the silverware lived up to its name, she began eyeing each other guest. They all ate without issue, smiling and gossiping amongst themselves without a care in the world.

Well, shit.

When Dean came up for air, she leaned over to whisper into his ear. “Dean, I don’t see any issue.”

“Well, I do—where the hell do they hide the salt?”

“Dean, focus.”

He turned to her, suddenly in full-on hunter mode. “What’s wrong?”

“The silverware’s real, right? No one’s having issues eating. And the domes things for the food seemed to be silver. That’d eliminate everyone here.”

His jade green eyes darted about the room quickly, widening minutely before he spoke again. “Not the waiters. They’re wearing gloves.”

She darted around to look where Dean was, and she saw a young woman topping off another guest’s wine glass, wearing crisp white gloves.

“Well, at least that narrows it down,” she mumbled.

“So, see, I had a reason to be suspicious of Jeeves.”

She turned back, her eyes narrowing in a playful glare.

He grinned victoriously, another taunt on his lips, when he was interrupted.

“What about you?”

The hunters turned to the woman sitting across from them, who had called attention to the hunters.

Shit.

The woman was in her late forties and looked quite good for her age. Her deep chocolate hair was swept up and away from her face, showing matching, kind eyes. Honestly, she was quite pretty. “What are you two whispering about over there? Nothing too scandalous, I should hope.”

Y/N smiled, trying to hide her mild panic. “In a room full of politicians, how can there be talk of anything scandalous?”

She was answered with polite laughter, and Dean gripped her hand under the table. He was never good at improv.

“Might I ask how you know the Governor?” she continued, and she looked a tiny bit more sinister. Perhaps she was trying to look so, or perhaps it was their own paranoia tainting their vision.

“My husband is a congressman,” Y/N grasped. “Twenty-second district.”

“Ah,” the woman smiled. “That sounds lovely. My husband,” she turned to the man on her right—a well-dressed man who looked slightly younger than she did, but no less handsome—and placed a hand on his shoulder. The man, who was deep in conversation with someone else, turned to his wife, offered a conciliatory smile, then went back to it. She continued, “Well, he’s a state senator.”

“That’s wonderful,” Y/N answered with what she hoped was a tone devoid of sarcasm. Last thing she needed was a pissing contest with some random woman.

The woman seemed placated. “Thank you. How long have you been a congressman?” she asked Dean.

Dean’s eyes widened comically. It didn’t help that his cheeks were stuffed with food in an effort to discourage any attempts to speak with him. Y/N had to bite back her laughter at the sight.

“I’m sorry?” he asked, the food in his mouth muffling his words.

The woman seemed sufficiently disgusted, but she continued. “Is this your first session, Congressman…?” she trailed off, obviously searching for a name.

It took a moment for him to remember which name he’d chosen for this case, time he took up by chewing slowly. “Hetfield. Dean Hetfield.”

“Congressman Hetfield,” she repeated. “A pleasure. I’m Sarah Finch.”

He nodded, a tight smile on his face. “This, uh, this is my wife, Y/N.”

Y/N, forced back into the conversation, smiled kindly. “It’s wonderful to meet you.”

“Likewise,” Sarah continued. “As I was saying, Congressman, how long have you been in your position?”

“Oh,” he laughed awkwardly. “Feels like I’ve been in this job for my entire life.”

She laughed politely. “Yes, my husband, Nathan, he often says the same thing. Are you a Democrat or a Republican?”

There was a beat before Dean answered. “I think that’s obvious, isn’t it?”

Sarah shrugged. “Ah, I suppose. I can’t imagine Alex would invite a Democrat into his home. He’s become more bipartisan in recent years, but the world has yet to end, has it?”

“Not for lack of trying,” Dean chuckled, tilting his head to the side awkwardly.

She gave a genuine laugh at that.

Y/N squeezed his hand under the table, trying to calm him down.

Thankfully, the servers came by with cake after that, the discussion flowed well enough for the rest of the meal.

“Still think pie would’ve been better,” Dean grumbled as they were released into the ballroom.

“Oh, stop complaining. You inhaled it, so I doubt the taste would’ve made a difference,” she countered as she twined their arms together.

He grumbled, “It’s the principle of the thing.”

She laughed at that, almost forgetting the reason that they were there.

Then the doors to the ballroom opened, revealing a beautiful room that looked more royal than anything she’d ever seen. Well, the Whitley family was old money, so maybe they were the American version of royalty.

However, in a room this big, their job would only get harder.

Dean quietly said the words that they were both thinking, “Well crap.”


End file.
